| Round of 64 | Kyle BattleSt. Norbert College vs. - | no result |
| Round of 64 | Can ThierhoffGustavus Adolphus College def. LuCas LeDouxGrinnell College | 6-3, 6-2 |
| Round of 64 | Tommy KeeneSaint John's University def. Bret LizotteBethel University | 7-6, 6-0 |
| Round of 64 | Brenden AmiotteSaint Mary's University def. Clay CregerMacalester | 6-2, 6-0 |
| Round of 64 | Jace MantheHamline University def. Augie BaduraUW-Eau Claire | 6-0, 6-2 |
| Round of 64 | Austin LaumbUW-Oshkosh def. Derek WilliamsNorthwestern (Minn.) | 6-3, 7-6, 10-5 |
| Round of 64 | Adam WieserSimpson College def. Kieran WallaceSt. Norbert College | 2-6, 6-3, 10-2 |
| Round of 64 | Matthew YangMacalester def. Joey ShubertUW-La Crosse | 6-1, 6-3 |
| Round of 64 | Nick WilliamsUW-La Crosse def. Peter SillsGrinnell College | 6-2, 6-1 |
| Round of 64 | Jacob DuxburyHamline University def. Sam GullickSt. Norbert College | 6-1, 6-1 |
| Round of 64 | Alex ZuzekSaint Mary's University def. Dexter JacksonBethany Lutheran College | 4-6, 6-0, 10-6 |
| Round of 64 | Kenny GoinsLuther College def. Joey EvavoldSaint John's University | 5-7, 7-6, 10-7 |
| Round of 64 | Matthew EngumConcordia Moorhead def. Joshua RamosCarroll University | 7-6, 6-3 |
| Round of 64 | Mark ConradCarleton College def. Reid LangeCornell College | 6-0, 6-0 |
| Round of 64 | Ben WordellWisconsin Luther College def. Brandon GlockEdgewood College | 7-5, 6-2 |
| Round of 64 | W Bryce GadkeSt Scholastica def. Jordan DullSt. Olaf | 6-2, 6-2 |
| Round of 64 | Alex VandenbergSt. Norbert College def. Blake OlmscheidSaint Mary's University | 6-3, 2-6, 12-10 |
| Round of 64 | Tom PrittinenSaint John's University def. Dalton WerckmanBethany Lutheran College | 6-3, 6-3 |
| Round of 64 | Travis BeachMacalester def. Cameron FairNorthwestern (Minn.) | 6-2, 6-0 |
| Round of 64 | Corey DuncanCornell College def. Carter LindnerHamline University | 2-6, 6-1, 10-8 |
| Round of 64 | Bernardo PradoUW-Eau Claire def. Kent SchallerBethel University | 6-0, 6-1 |
| Round of 64 | David SchneckConcordia Moorhead def. Mitchell ToboyekCarroll University | 6-2, 6-1 |
| Round of 64 | Sam GowanUW-La Crosse def. Joe OleniczakSt. Norbert College | 6-0, 6-1 |
| Round of 64 | Beau BresslerGrinnell College def. Jordan AndersenUW-Oshkosh | 6-3, 6-1 |
| Round of 64 | Billy KavanaghSt. Norbert College def. Auston SackCornell College | 6-1, 6-1 |
| Round of 64 | L William O'ConnellUW-Oshkosh def. Trace CombsSt Scholastica | 6-2, 2-6, 10-8 |
| Round of 64 | J.J. JanssenGustavus Adolphus College def. Jordan PoffBethany Lutheran College | 6-0, 6-0 |
| Round of 64 | Peter RietgrafSimpson College def. Christian YunSt. Olaf | 6-2, 7-6 |
| Round of 64 | Ryan MegerSaint John's University def. Cash RodemakerBethel University | 6-2, 6-2 |
| Round of 64 | Dylan ManetterUW-La Crosse def. Hunter AntonisseGrinnell College | 6-1, 6-1 |
| Round of 64 | Landon RidpathNorthwestern (Minn.) def. John BanovetzHamline University | 6-4, 6-4 |
| Round of 64 | Jake SmithLuther College def. Tejas SinghMacalester | 6-0, 6-1 |
| Round of 64 | Alex BrostUW-La Crosse def. Adam BuschLawrence College | 5-7, 6-0, 12-10 |
| Round of 32 | Can ThierhoffGustavus Adolphus College def. Kyle BattleSt. Norbert College | 6-4, 6-1 |
| Round of 32 | Brenden AmiotteSaint Mary's University def. Tommy KeeneSaint John's University | 6-2, 6-3 |
| Round of 32 | Augie BaduraUW-Eau Claire def. Austin LaumbUW-Oshkosh | 6-1, 6-1 |
| Round of 32 | Matthew YangMacalester def. Adam WieserSimpson College | 6-0, 6-1 |
| Round of 32 | Nick WilliamsUW-La Crosse def. Jacob DuxburyHamline University | 6-2, 6-2 |
| Round of 32 | Kenny GoinsLuther College def. Alex ZuzekSaint Mary's University | 5-7, 6-2, 11-9 |
| Round of 32 | Mark ConradCarleton College def. Matthew EngumConcordia Moorhead | 6-3, 6-4 |
| Round of 32 | W Bryce GadkeSt Scholastica def. Ben WordellWisconsin Luther College | 6-0, 6-1 |
| Round of 32 | Tom PrittinenSaint John's University def. Alex VandenbergSt. Norbert College | 6-1, 6-7, 10-8 |
| Round of 32 | Travis BeachMacalester def. Corey DuncanCornell College | 6-1, 6-3 |
| Round of 32 | Bernardo PradoUW-Eau Claire def. David SchneckConcordia Moorhead | 6-4, 7-6 |
| Round of 32 | Beau BresslerGrinnell College def. Sam GowanUW-La Crosse | 6-3, 1-6, 11-9 |
| Round of 32 | Billy KavanaghSt. Norbert College def. William O'ConnellUW-Oshkosh | 6-1, 6-2 |
| Round of 32 | J.J. JanssenGustavus Adolphus College def. Peter RietgrafSimpson College | 6-3, 6-2 |
| Round of 32 | Ryan MegerSaint John's University def. Dylan ManetterUW-La Crosse | 6-2, 6-2 |
| Round of 32 | Jake SmithLuther College def. Landon RidpathNorthwestern (Minn.) | 6-2, 6-1 |
| Round of 16 | Can ThierhoffGustavus Adolphus College def. Brenden AmiotteSaint Mary's University | 2-6, 6-1, 10-7 |
| Round of 16 | Augie BaduraUW-Eau Claire def. Matthew YangMacalester | 6-1, 6-3 |
| Round of 16 | Nick WilliamsUW-La Crosse def. Kenny GoinsLuther College | 6-4, 6-2 |
| Round of 16 | L Mark ConradCarleton College def. Bryce GadkeSt Scholastica | 7-6, 6-3 |
| Round of 16 | Travis BeachMacalester def. Tom PrittinenSaint John's University | 6-2, 6-0 |
| Round of 16 | Bernardo PradoUW-Eau Claire def. Beau BresslerGrinnell College | 6-1, 7-6 |
| Round of 16 | J.J. JanssenGustavus Adolphus College def. Billy KavanaghSt. Norbert College | 6-1, 6-1 |
| Round of 16 | Jake SmithLuther College def. Ryan MegerSaint John's University | 6-4, 6-3 |
| Quarterfinal | Augie BaduraUW-Eau Claire def. Can ThierhoffGustavus Adolphus College | 6-3, 6-1 |
| Quarterfinal | Mark ConradCarleton College def. Nick WilliamsUW-La Crosse | 6-0, 6-0 |
| Quarterfinal | Bernardo PradoUW-Eau Claire def. Travis BeachMacalester | 6-1, 6-2 |
| Quarterfinal | Jake SmithLuther College def. J.J. JanssenGustavus Adolphus College | 6-3, 6-7, 6-2 |
| Semifinal | Mark ConradCarleton College def. Augie BaduraUW-Eau Claire | 6-3, 6-1 |
| Semifinal | Bernardo PradoUW-Eau Claire def. Jake SmithLuther College | 6-4, 6-4 |
| Final | Mark ConradCarleton College def. Bernardo PradoUW-Eau Claire | 6-2, 6-2 |
| Round of 64 | Danny SchoenUW-Eau Claire def. Matthew BrooksUW-Oshkosh | 6-0, 6-0 |
| Round of 64 | Caleb UlringGrinnell College def. Tanner MagruderNorthwestern (Minn.) | 1-0 |
| Round of 64 | Robert SpieringConcordia Wisconsin def. Zach SimonetSt. Norbert College | 6-2, 6-1 |
| Round of 64 | Pierce CareySimpson College def. Danny HoganSt. Olaf | 6-1, 6-2 |
| Round of 64 | Henry MorrisBethel University def. Ben WilsonMacalester | 5-7, 6-4, 10-8 |
| Round of 64 | W Jordan LindholmSt Scholastica def. Scott SchwandtConcordia Moorhead | 6-1, 7-6 |
| Round of 64 | Michael ThompsonSaint John's University def. Alex HolmSaint Mary's University | 6-4, 6-0 |
| Round of 64 | Jonah PunnooseSaint John's University def. Ben EksteinHamline University | 6-3, 6-2 |
| Round of 64 | Simon BrandtUW-La Crosse def. Matthew VoissemSt. Norbert College | 6-0, 6-1 |
| Round of 64 | Camden LongLuther College def. Joshua KimballNorthwestern (Minn.) | 3-6, 6-0, 10-4 |
| Round of 64 | Jesse SchneedbergerConcordia Moorhead def. Alex RandCornell College | 6-0, 6-2 |
| Round of 64 | Warren LawrenzSaint Mary's University def. Peter LindbergBethel University | 6-1, 6-4 |
| Round of 64 | Adam HawleyUW-Oshkosh def. Matt La VioletteSt. Norbert College | 6-3, 7-6 |
| Round of 64 | Ameer SujjahGrinnell College def. Ian FosterCarroll University | 6-2, 6-2 |
| Round of 64 | Alex SenjemGustavus Adolphus College def. Carter DahlBethany Lutheran College | 6-1, 6-3 |
| Round of 64 | Brett GiesenSaint Mary's University def. Mark HruskaEdgewood College | 6-0, 6-1 |
| Round of 64 | Jared BarnesLuther College def. Ben KlimekHamline University | 6-0, 6-2 |
| Round of 64 | Zach LaneGrinnell College def. David LefflerUW-Oshkosh | 6-2, 6-2 |
| Round of 64 | Blake YoungbergCarroll University def. Jacob KublerBethany Lutheran College | 4-6, 7-5, 10-3 |
| Round of 64 | L Corey LokenSt. Olaf def. Zach MeikleSt Scholastica | 6-0, 6-0 |
| Round of 64 | Derek SallmannWisconsin Luther College def. Quinn BlodgettNorthwestern (Minn.) | 6-2, 6-0 |
| Round of 64 | Caleb PerkinsBethel University def. Austin StormConcordia Moorhead | 6-1, 2-6, 10-6 |
| Round of 64 | Medkim DejeneUW-La Crosse def. Tim FifarekSt. Norbert College | 6-1, 6-0 |
| Round of 64 | Sam PhillipsUW-Eau Claire def. Robbie StevensBethany Lutheran College | 6-3, 6-1 |
| Round of 64 | Joey RobertsonGrinnell College def. Grahamm KelloggGustavus Adolphus College | 6-1, 6-1 |
| Round of 64 | Hunter KrebsbachSaint John's University def. Kahlo VueSt. Norbert College | 6-2, 6-1 |
| Round of 64 | Peter WillenborgMacalester def. Sam PetersonHamline University | 6-4, 6-1 |
| Round of 64 | Fumiya KitaharaWartburg College def. Andrew ReinemannSt. Norbert College | 6-4, 7-5 |
| Round of 64 | Hunter FerneliusBethel University def. Samuel DeetzLuther College | 6-1, 6-0 |
| Round of 64 | Morgan RossCarleton College def. Tom GreeneCornell College | 6-1, 6-2 |
| Round of 64 | Steven LeeUW-La Crosse def. Garen MerrittSaint Mary's University | 6-3, 6-0 |
| Round of 32 | Danny SchoenUW-Eau Claire def. Alex BrostUW-La Crosse | 6-0, 6-0 |
| Round of 32 | Caleb UlringGrinnell College def. Robert SpieringConcordia Wisconsin | 6-4, 6-4 |
| Round of 32 | Pierce CareySimpson College def. Henry MorrisBethel University | 6-4, 6-1 |
| Round of 32 | L Alex HolmSaint Mary's University def. Jordan LindholmSt Scholastica | 6-2, 6-4 |
| Round of 32 | Jonah PunnooseSaint John's University def. Simon BrandtUW-La Crosse | 4-6, 6-4, 10-7 |
| Round of 32 | Camden LongLuther College def. Jesse SchneedbergerConcordia Moorhead | 6-3, 7-5, 3-10 |
| Round of 32 | Warren LawrenzSaint Mary's University def. Adam HawleyUW-Oshkosh | 6-3, 6-4 |
| Round of 32 | Alex SenjemGustavus Adolphus College def. Ameer SujjahGrinnell College | 6-4, 6-2 |
| Round of 32 | Brett GiesenSaint Mary's University def. Jared BarnesLuther College | 4-6, 6-4, 13-11 |
| Round of 32 | Zach LaneGrinnell College def. Blake YoungbergCarroll University | 6-2, 6-1 |
| Round of 32 | Corey LokenSt. Olaf def. Derek SallmannWisconsin Luther College | 6-1, 6-4 |
| Round of 32 | Medkim DejeneUW-La Crosse def. Caleb PerkinsBethel University | 7-6, 6-3 |
| Round of 32 | Joey RobertsonGrinnell College def. Sam PhillipsUW-Eau Claire | 6-0, 6-0 |
| Round of 32 | Hunter KrebsbachSaint John's University def. Peter WillenborgMacalester | 6-1, 6-7, 10-5 |
| Round of 32 | Hunter FerneliusBethel University def. Fumiya KitaharaWartburg College | 4-6, 6-0, 10-8 |
| Round of 32 | Morgan RossCarleton College def. Steven LeeUW-La Crosse | 6-1, 6-0 |
| Round of 16 | Danny SchoenUW-Eau Claire def. Caleb UlringGrinnell College | 6-0, 6-0 |
| Round of 16 | Pierce CareySimpson College def. Alex HolmSaint Mary's University | 6-0, 6-0 |
| Round of 16 | Jonah PunnooseSaint John's University def. Jesse SchneedbergerConcordia Moorhead | 6-4, 6-3 |
| Round of 16 | Alex SenjemGustavus Adolphus College def. Warren LawrenzSaint Mary's University | 6-1, 4-6, 10-3 |
| Round of 16 | Zach LaneGrinnell College def. Brett GiesenSaint Mary's University | 6-2, 6-1 |
| Round of 16 | Medkim DejeneUW-La Crosse def. Corey LokenSt. Olaf | 6-1, 6-3 |
| Round of 16 | Hunter KrebsbachSaint John's University def. Joey RobertsonGrinnell College | 6-2, 6-3 |
| Round of 16 | Hunter FerneliusBethel University def. Morgan RossCarleton College | 6-1, 6-2 |
| Quarterfinal | Danny SchoenUW-Eau Claire def. Pierce CareySimpson College | 6-2, 6-3 |
| Quarterfinal | Jonah PunnooseSaint John's University def. Alex SenjemGustavus Adolphus College | 6-2, 6-2 |
| Quarterfinal | Zach LaneGrinnell College def. Medkim DejeneUW-La Crosse | 6-4, 6-7, 6-1 |
| Quarterfinal | Hunter FerneliusBethel University def. Hunter KrebsbachSaint John's University | 5-7, 6-4, 6-1 |
| Semifinal | Danny SchoenUW-Eau Claire def. Jonah PunnooseSaint John's University | 6-2, 6-3 |
| Semifinal | Hunter FerneliusBethel University def. Zach LaneGrinnell College | 5-7, 6-4, 6-1 |
| Final | Danny SchoenUW-Eau Claire def. Hunter FerneliusBethel University | 6-4, 6-1 |
| Final | Mark ConradCarleton College def. Danny SchoenUW-Eau Claire | 6-4, 6-7, 6-4 |
